JPH0222761B2 - - Google Patents
Info
- Publication number
- JPH0222761B2 JPH0222761B2 JP57045692A JP4569282A JPH0222761B2 JP H0222761 B2 JPH0222761 B2 JP H0222761B2 JP 57045692 A JP57045692 A JP 57045692A JP 4569282 A JP4569282 A JP 4569282A JP H0222761 B2 JPH0222761 B2 JP H0222761B2
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- polymerization
- mol
- maleimide
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000178 monomer Substances 0.000 claims description 88
- 229920001577 copolymer Polymers 0.000 claims description 70
- 238000006116 polymerization reaction Methods 0.000 claims description 49
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 39
- 229920002554 vinyl polymer Polymers 0.000 claims description 28
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 56
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 25
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 17
- 238000007334 copolymerization reaction Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920005603 alternating copolymer Polymers 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 238000010557 suspension polymerization reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- -1 polyethylene terephthalate Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 2
- 229940096992 potassium oleate Drugs 0.000 description 2
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 2
- 229920006163 vinyl copolymer Polymers 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- QDOXQIRWYQMOKT-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione;styrene Chemical compound C=CC1=CC=CC=C1.O=C1C=CC(=O)N1C1=CC=CC=C1 QDOXQIRWYQMOKT-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- UIZDKHDPZRCOBN-UHFFFAOYSA-N 3-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCC1=CC(=O)NC1=O UIZDKHDPZRCOBN-UHFFFAOYSA-N 0.000 description 1
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
- 235000010893 Bischofia javanica Nutrition 0.000 description 1
- 240000005220 Bischofia javanica Species 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- YPMFVRISQCBINL-UHFFFAOYSA-L S([O-])[O-].C(=O)N.[Na+].[Na+] Chemical compound S([O-])[O-].C(=O)N.[Na+].[Na+] YPMFVRISQCBINL-UHFFFAOYSA-L 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
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Claims (1)
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4569282A JPS58162616A (ja) | 1982-03-24 | 1982-03-24 | ãã¬ã€ããç³»å ±éåäœã®è£œé æ¹æ³ |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4569282A JPS58162616A (ja) | 1982-03-24 | 1982-03-24 | ãã¬ã€ããç³»å ±éåäœã®è£œé æ¹æ³ |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58162616A JPS58162616A (ja) | 1983-09-27 |
JPH0222761B2 true JPH0222761B2 (ja) | 1990-05-21 |
Family
ID=12726433
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4569282A Granted JPS58162616A (ja) | 1982-03-24 | 1982-03-24 | ãã¬ã€ããç³»å ±éåäœã®è£œé æ¹æ³ |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58162616A (ja) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61162507A (ja) * | 1985-01-11 | 1986-07-23 | Sumitomo Naugatuck Co Ltd | èç±æ§ãªãã³ã«æµåæ§ã«åªããå ±éåäœã®è£œé æ³ |
JPS61176501U (ja) * | 1985-04-22 | 1986-11-04 | ||
JPS62209110A (ja) * | 1985-04-30 | 1987-09-14 | Nippon Shokubai Kagaku Kogyo Co Ltd | èç±æ§åŸ®çŽ°æš¹èç²åã®åæ£æ¶²ã®è£œæ³ |
JPS61250008A (ja) * | 1985-04-30 | 1986-11-07 | Nippon Shokubai Kagaku Kogyo Co Ltd | èç±æ§åŸ®çŽ°æš¹èç²åã®è£œæ³ |
US4757109A (en) * | 1985-05-16 | 1988-07-12 | Mitsubishi Rayon Co., Ltd. | Process for the preparation of maleimide copolymers and thermoplastic resin composition using the same |
JPS61264011A (ja) * | 1985-05-16 | 1986-11-21 | Mitsubishi Rayon Co Ltd | èç±æ§æš¹èã®è£œæ³ |
JPH0762099B2 (ja) * | 1985-05-17 | 1995-07-05 | äžè±ã¬ã€ãšã³æ ªåŒäŒç€Ÿ | æš¹èçµæç©ã®è£œæ³ |
US5191046A (en) * | 1985-06-03 | 1993-03-02 | Mitsui Toatsu Chemicals, Incorporated | Transparent heat-resistant styrene-base copolymer |
JPS62236809A (ja) * | 1986-04-08 | 1987-10-16 | Denki Kagaku Kogyo Kk | å¡©åããã«ç³»æš¹èã®è£œé æ¹æ³ |
JPS6390515A (ja) * | 1986-10-03 | 1988-04-21 | Mitsubishi Monsanto Chem Co | èç±æ§æš¹èçµæç©ã®è£œé æ¹æ³ |
JPS63182309A (ja) * | 1987-01-22 | 1988-07-27 | Ube Saikon Kk | ç±å¯å¡æ§èç±æš¹èã®è£œé æ¹æ³ |
JP2600784B2 (ja) * | 1987-06-12 | 1997-04-16 | äœåååŠå·¥æ¥æ ªåŒäŒç€Ÿ | è³éŠæããã«ç³»æš¹èæ圢äœã®è£œé æ¹æ³ |
AU617206B2 (en) * | 1988-08-15 | 1991-11-21 | Mitsubishi Rayon Company Limited | Maleimide copolymer and a process for producing the same |
AU613802B2 (en) * | 1988-10-31 | 1991-08-08 | Mitsubishi Rayon Company Limited | Heat resistant and impact resistant resin composition |
JP2840645B2 (ja) * | 1988-11-08 | 1998-12-24 | é»æ°ååŠå·¥æ¥æ ªåŒäŒç€Ÿ | èç±æ§ç±å¯å¡æ§æš¹èåã³ãã®è£œé æ¹æ³ |
TW197454B (ja) * | 1991-04-15 | 1993-01-01 | Catalyst co ltd | |
JP2716598B2 (ja) * | 1991-04-15 | 1998-02-18 | æ ªåŒäŒç€Ÿæ¥æ¬è§Šåª | ãã¬ã€ããç³»å ±éåäœã®è£œé æ¹æ³ |
DE69302523T2 (de) * | 1992-06-17 | 1997-01-16 | Nippon Catalytic Chem Ind | Copolymer auf Basis von Maleimid und Verfahren zu seiner Herstellung |
JP2665302B2 (ja) * | 1992-09-11 | 1997-10-22 | æ ªåŒäŒç€Ÿæ¥æ¬è§Šåª | ãã¬ã€ããç³»å ±éåäœããã®è£œé æ¹æ³ããã³ãããå«ãç±å¯å¡æ§æš¹èçµæç© |
US6100366A (en) * | 1998-09-18 | 2000-08-08 | Nippon Shokubai Co., Ltd. | Cyclic imino ether group containing polymer and production process therefor |
WO2008038857A1 (en) | 2006-09-28 | 2008-04-03 | Korea Kumho Petrochemical Co., Ltd | Maleimide-alpha-alkylstyrene-based tetrapolymer with low molten viscosity and continuous bulk process for producing it |
TW200940568A (en) | 2008-02-28 | 2009-10-01 | Toray Industries | Method of producing thermal plastic copolymer |
KR101686284B1 (ko) * | 2013-12-06 | 2016-12-13 | 죌ìíì¬ ìì§íí | ëŽìŽì± ê³µì€í© ìì§ì ì ì¡°ë°©ë² ë° ìŽë¥Œ ìŽì©íì¬ ì ì¡°í ê³µì€í© ìì§ |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2971939A (en) * | 1959-01-30 | 1961-02-14 | Monsanto Chemicals | Process for preparing homogeneous copolymers of a vinylidene monomer and a maleic monomer and product thereof |
JPS5493091A (en) * | 1977-11-15 | 1979-07-23 | Rhone Poulenc Ind | Styrene polymer having improved thermal properties |
JPS57167341A (en) * | 1981-04-08 | 1982-10-15 | Asahi Chem Ind Co Ltd | Thermoplastic resin composition |
-
1982
- 1982-03-24 JP JP4569282A patent/JPS58162616A/ja active Granted
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2971939A (en) * | 1959-01-30 | 1961-02-14 | Monsanto Chemicals | Process for preparing homogeneous copolymers of a vinylidene monomer and a maleic monomer and product thereof |
JPS5493091A (en) * | 1977-11-15 | 1979-07-23 | Rhone Poulenc Ind | Styrene polymer having improved thermal properties |
JPS57167341A (en) * | 1981-04-08 | 1982-10-15 | Asahi Chem Ind Co Ltd | Thermoplastic resin composition |
Also Published As
Publication number | Publication date |
---|---|
JPS58162616A (ja) | 1983-09-27 |
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